Tetrahydrofuran → HCID 58312744, compound

HRID 1751179Notes

Reaction equation

HRID 1751179 reaction equation
CS[C:3]1[N:8]=[C:7](/[CH:9]=[C:10]2/[C:11](=[O:16])[NH:12][C:13](=[O:15])[S:14]/2)[CH:6]=[CH:5][N:4]=1.O[O:18][S:19]([O-:21])=O.[K+].[CH2:23]1COCC1>O>[CH3:23][S:19]([C:3]1[N:8]=[C:7](/[CH:9]=[C:10]2/[C:11](=[O:16])[NH:12][C:13](=[O:15])[S:14]/2)[CH:6]=[CH:5][N:4]=1)(=[O:21])=[O:18]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 58312726HCID 58312726, compound

Product 1

HCID 58312744HCID 58312744, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (Z)-5-((2-(methylthio)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione (5) (3.5 g, 13.82 mmol) in THF (100 mL, 0.13 M) was treated with a solution of oxone (25.8 g, 41.5 mmol, 3.0 equiv.) in water (175 mL). The resulting mixture was stirred at room temperature for 48 h. The resulting precipitate was filtered and washed with water (20 mL) and diethyl ether (20 mL) to afford (Z)-5-((2-(methylsulfonyl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione (6) as a solid (2.48 g, 3.94 g theoretical, 63%). LC-MS m/z 286 (M+1).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water (20 mL) and diethyl ether (20 mL)

Sources & evidence

ORD record
ord-567a9bd8597d4fb4b58b0df5b7e3fc32
Source dataset
uspto-grants-2015_10
Patent number
US09157077B2

Reaction notes

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